Extraction of 5-Hydroxymethylfurfural and Furfural in Aqueous Biphasic Systems: A COSMO-RS Guided Approach to Greener Solvent Selection

Autor(es)

Soukup-Carne, Dominik ; Lopez-Porfiri, Pablo ; Bragagnolo, Felipe Sanchez ; Funari, Cristiano Soleo ; Fan, Xiaolei ; Gonzalez-Miquel, Maria ; Esteban, Jesus

• Tipo de documento: Artigo Científico
• Fonte: ACS SUSTAINABLE CHEMISTRY & ENGINEERING; v. 12, n. 9, p. 14-pg., 2024-02-20.

Resumo

5-Hydroxymethylfurfural (HMF) and furfural (Fur) are promising biobased platform chemicals, derived from the dehydration of carbohydrate feedstocks, normally conducted in an aqueous phase. Plagued by side-reactions in such phase, such as the rehydration to levulinic acid (LA) and formic acid (FA) or self-condensation to humins, HMF and Fur necessitates diversification from monophasic aqueous reaction systems toward biphasic systems to mitigate undesired side-reactions. Here, a methodology based on the COnductor-like Screening MOdel for Real Solvents (COSMO-RS) method was used to screen solvent candidates based on the predicted partition coefficients (K-i). Hansen solubility parameters in conjunction with excess thermodynamic quantities determined by COSMO-RS were employed to assess solvent compatibility. Experimental validation of the COSMO-RS values highlighted only minor deviations from the predictions with root-mean-square-error (RMSE) values of HMF and Fur at 0.76 and 5.32, respectively, at 298 K. The combined effort suggested cyclohexanone, isophorone, and methyl isobutyl ketone (MIBK) as the best candidates. Finally, extraction solvent reuse demonstrated cyclohexanone suitability for HMF extraction with K-HMF of 3.66 and MIBK for Fur with K-Fur 7.80 with consistent partitioning across four total runs. Both solvents are classified as recommended by the CHEM21 solvent selection guide, hence adding to the sustainability of the process. (AU)

• Processo FAPESP: 22/00645-0 - Valorização integral de subprodutos de soja e de trigo gerados no Brasil e no Reino Unido: uma abordagem de agregação de valor em cascata
• Beneficiário: Cristiano Soleo de Funari
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 17/06216-6 - Desenvolvimento de metodologias analíticas verdes na busca por compostos orgânicos de alto valor agregado em resíduos agrícolas
• Beneficiário: Cristiano Soleo de Funari
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores
• Processo FAPESP: 22/10469-5 - Aplicação de ferramentas in silico para a extração de compostos bioativos de subprodutos agrícolas por meio de líquidos expandidos por gás e solventes alternáveis e verdes
• Beneficiário: Felipe Sanchez Bragagnolo
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado